It is known in the art that both the amino and the hydroxy group are ortho and para directing. It is also known that when both groups are on an aryl ring, substitution reactions generally lead to a mixture of ortho and para isomers, and frequently to polysubstituted products. Needless to say, the formation and separation of isomeric mixtures greatly reduces product yields. For example, the synthesis of 2-amino-5-methylphenol involves only two reaction steps: (1) nitration of 3-methylphenol (meta-cresol) and (2) reduction of the nitro intermediate. However, the overall yield is very poor (less than 30%), due to the formation of other nitro isomers and the need to separate this mixture by steam distillation.
It is known in the art that 5-substituted-2-aminophenols are useful intermediates, for example, in the photographic industry. Unfortunately, this type of compound is generally hard to make in pure form and in good yield, for the reasons stated above.